CN105815326B - Preparation method and application of agricultural bactericide containing parthenolide - Google Patents
Preparation method and application of agricultural bactericide containing parthenolide Download PDFInfo
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- CN105815326B CN105815326B CN201610138008.3A CN201610138008A CN105815326B CN 105815326 B CN105815326 B CN 105815326B CN 201610138008 A CN201610138008 A CN 201610138008A CN 105815326 B CN105815326 B CN 105815326B
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- BUQLXKSONWUQAC-UHFFFAOYSA-N Parthenolide Natural products CC1C2OC(=O)C(=C)C2CCC(=C/CCC1(C)O)C BUQLXKSONWUQAC-UHFFFAOYSA-N 0.000 title claims abstract description 45
- KTEXNACQROZXEV-PVLRGYAZSA-N parthenolide Chemical compound C1CC(/C)=C/CC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]21 KTEXNACQROZXEV-PVLRGYAZSA-N 0.000 title claims abstract description 45
- 229940069510 parthenolide Drugs 0.000 title claims abstract description 45
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 19
- 239000003899 bactericide agent Substances 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 230000001580 bacterial effect Effects 0.000 claims abstract description 21
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to a botanical pesticide bactericide and a preparation method thereof. The bactericide is prepared by extracting and processing whole plant of feverfew. Wherein the weight percentage of the main active components is as follows: 5-20% of parthenolide, water and a surfactant are prepared into an aqueous emulsion, and the aqueous emulsion is diluted and used for preventing and treating various crop diseases. The invention has the advantages that: the biological pesticide has the advantages of easily available raw materials, simple process and low cost, has better control effect on various diseases such as rice bacterial leaf blight, rice bacterial leaf streak, corn small leaf spot and the like, is safe to crops, does not pollute the environment, and is a biological pesticide preparation suitable for the production requirement of pollution-free agricultural products in China.
Description
Technical Field
The invention relates to an agricultural fungicide containing parthenolide and a preparation method thereof.
Background
At present, more than 80% of pesticides used in China are chemical pesticides, the use of the chemical pesticides greatly promotes the development of modern agriculture, but with the remarkable improvement of grain yield, people pay more and more attention to grain safety problems and environmental problems brought by the use of the chemical pesticides, so that the research of the fields of pollution-free biological pesticide industry and biological control obtains an inexhaustible development opportunity. A new pesticide is discovered and developed by a traditional method, tens of thousands of new compounds need to be screened or even more, the cost is huge, and the period is long. The method for separating and screening the lead compound with strong activity from organisms, particularly plants, has the advantages of relatively low cost, strong pertinence and short development period, and the developed pesticide has the advantages of environmental friendliness, relative safety to non-target organisms, specific action mode, difficult generation of drug resistance, easy degradation in natural environment, no residue and the like, and is an ideal pesticide for developing organic agriculture and promoting agricultural sustainable development.
Parthenolide is a sesquiterpene lactone compound derived from plants of the Compositae or Magnoliaceae, and mainly comprises three isoprene units and a lactone group. In the past years, parthenolide has been of interest due to its anti-inflammatory activity, and until 1973 parthenolide was first discovered to have anti-tumor activity and is a potential novel anti-tumor drug, and subsequent studies have demonstrated that parthenolide is cytotoxic to a variety of cancer cells, including breast cancer, colorectal cancer, pancreatic cancer, prostate cancer, myeloma, leukemia, and the like. At present, parthenolide has been applied in the field of medicine for treating skin infection, rheumatism, migraine and the like, and can inhibit tumor cell proliferation. The research already shows that parthenolide has certain in vitro inhibitory effect on some plant pathogenic fungi, oomycetes, bacteria and even viruses, but the activity research objects are few, and the parthenolide is not developed as an agricultural bactericide. The invention provides a preparation method of an agricultural fungicide containing parthenolide and application of the agricultural fungicide to prevention and treatment of common plant diseases which are not related in the existing research reports.
Disclosure of Invention
The invention aims to provide a preparation method and application of an agricultural bactericide containing parthenolide.
The parthenolide bactericide is characterized in that the bactericide takes parthenolide as a main active ingredient, the content of the parthenolide is 5-20%, and the parthenolide bactericide comprises the following components in percentage by weight:
5-20% of parthenolide
70 to 90 percent of water
5-10% of surfactant
The parthenolide bactericide is prepared by the following preparation method:
a. placing the whole feverfew in an extraction kettle, adding 3-10 times of crude drug volume of lower alcohol, wherein the lower alcohol is C1-C5 alcohol, the concentration of the lower alcohol is 50-95%, the extraction temperature is 30-80 ℃, filtering to obtain filtrate, repeatedly extracting for 1-4 times, and combining the filtrates to obtain crude extract;
b. concentrating the crude extract to 1/3, adsorbing with macroporous adsorption resin, washing with water soluble impurities with 1 column volume, washing with 30% ethanol with 2 column volumes, gradient eluting with 45% -85% ethanol, and collecting eluate, wherein the macroporous resin is type D101, HP-20 or AB-8;
c. concentrating the eluate under reduced pressure to obtain fluid extract without organic solvent smell, and repeatedly passing through silica gel or spherical silica gel, low pressure and medium pressure column chromatography; separating and purifying by gel column chromatography and recrystallization (ethyl acetate-methanol) to obtain parthenolide with purity of more than 90%;
d. firstly, mixing a surfactant and parthenolide in a homogenizer, adding water into the homogenizer while stirring at the temperature of 30-50 ℃, stirring for 30 minutes, and cooling to normal temperature to form an aqueous emulsion, thus obtaining a parthenolide bactericide;
wherein the structure of parthenolide is as follows:
when in use, the water can be added to dilute the mixture into different concentrations according to the requirement and then the mixture is sprayed for use.
The invention has the advantages that: 1. the results of indoor and greenhouse experiments show that the product has good inhibitory activity on various plant pathogenic bacteria such as rice bacterial blight, rice bacterial streak germ, corn microsporum and the like. 2. The product has the advantages of easily obtained raw materials, simple processing, low requirement on equipment and economic use. The product is processed without special equipment, the main processing process comprises extraction, concentration and mixing, and common pesticide enterprises can process the product. 3. The product of the invention is safe to the environment. The main raw materials of the bactericide are from plants, are safe to the environment and non-target organisms, and are a biopesticide preparation suitable for the production requirement of pollution-free agricultural products in China.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments, but the present invention is not limited to only the illustrated embodiments.
Example 1
5kg of feverfew whole plant is extracted by reflux for 3 times at 60 ℃ by using 75% ethanol to obtain a total extract, the total extract is absorbed by A8 macroporous resin, is respectively eluted by using water, 30%, 45%, 60% and 90% ethanol, the 45%, 60% and 95% elution parts of the macroporous resin are collected, and the eluent is concentrated to 1.5 kg of fluid extract to obtain the extract containing parthenolide. Repeatedly passing the extract through silica gel column chromatography; separating and purifying by gel column chromatography and recrystallization (ethyl acetate-methanol) to obtain parthenolide with purity of more than 90%; placing 0.5kg surfactant (such as polysorbate-80) and parthenolide in a homogenizer, heating to 30 deg.C, adding 1kg water into the homogenizer while stirring, stirring for 30 min, mixing, cooling to room temperature to obtain water emulsion to obtain parthenolide bactericide.
Example 2
10 kg of feverfew whole plant is extracted by reflux for 3 times at 60 ℃ by 95 percent ethanol to obtain a total extract, the total extract is absorbed by D101 macroporous resin, is respectively eluted by water, 30 percent, 45 percent and 85 percent ethanol, the 45 percent and 85 percent elution parts of the macroporous resin are collected, the eluent is concentrated to 3.0 kg of fluid extract, and the fluid extract is repeatedly subjected to silica gel column chromatography; separating and purifying by gel column chromatography and recrystallization (ethyl acetate-methanol) to obtain parthenolide with purity of more than 90%; placing 0.5kg surfactant (such as polyoxyethylene nonionic surfactant: OP-10) and parthenolide in a homogenizer, heating to 50 deg.C, adding 1kg water into the homogenizer while stirring, stirring for 30 min, mixing, cooling to room temperature to obtain parthenolide bactericide in the form of water emulsion.
Example 3
The parthenolide fungicide prepared according to the example 1 is measured by the antibiogram:
the pathogenic bacteria of the test plant include Sclerotinia sclerotiorum (A)Sclerotinia sclerotiorum) Wheat scab bacteria (1)Fusarium graminearum) Cucumber Botrytis cinerea: (Botrytis cinerea) Grape anthracnose bacteria (1)Colletotrichum gloeosporioides) Rhizoctonia solani (C. solani)Rhizoctonia solani) Corn leaf spot bacteria (1)Helminthosporium maydis) Botrytis cinerea (Fragile cinerea) (A. fragrans)Botrytis cinerea) Bacterial blight of rice (1)Fusarium moniliforme) Rhizoctonia cerealis (Rhizoctonia cerealis) Tomato early blight bacterium (A), (B), (C)Alternaria solani) Cotton verticillium wilt bacteria (A), (B)Verticillium dahliae) Magnaporthe grisea (A)Magnaporthe oryzae) Phytophthora capsici (Leyss. sp.), (Phytophthora capsici) Phytophthora sojae (A) and (B)Phytophthora sojae) Bacterial blight of rice (1)Xanthomonas oryzaepv.oryzae) Bacterial leaf streak disease of rice (1)Xanthomonas oryzaepv.oryzicola) Cabbage black rot bacteria (A), (B), (C)Xanthomonas campestrispv.campestris) And 15 common plant pathogenic bacteria. All tested pathogens were field-collected isolates.
The method adopts a hypha growth rate method (fungi and oomycetes) or a turbidity method (bacteria) to carry out the preliminary indoor toxicity measurement on the 15 plant pathogenic bacteria. Activating and culturing each strain on a PDA (fungi), V8 (oomycetes) plate or an NB (bacteria) culture solution, punching a bacterial disc on the edge of a bacterial colony by using a puncher with the caliber of 5mm for the fungi and the oomycetes, preparing a mother solution of a test bactericide by using sterile water, adding the mother solution into a culture medium to prepare a PDA or V8 drug-containing plate with the final concentration of 10 mu g/mL of parthenolide, inoculating each pathogenic bacterial disc onto the plate, and treating 3 times by using the sterile water as a control; for bacteria, diluting the bacterial liquid to a certain turbidity, adding the diluted bacterial liquid into NB liquid culture medium with the final concentration of 10 mug/mL of parthenolide, and repeating the treatment for 3 times by taking sterile water as a control; culturing in 25 deg.C incubator until the control is close to the full plate (fungus, oomycetes) or shaking at 28 deg.C to the logarithmic growth phase (bacteria), measuring colony diameter (fungus, oomycetes) by cross method or measuring turbidity (bacteria) by turbidimeter, and calculating the inhibition rate.
Test results
The final concentration of parthenolide fungicide prepared according to example 1 in the culture medium was 10. mu.g/mL, and the inhibitory activity against various plant pathogenic fungi was shown in Table 1. As can be seen from the results in the table, the parthenolide fungicide produced according to the technology of the invention has good inhibition effect on various pathogenic bacteria to be tested.
TABLE 1 inhibition of plant pathogens by parthenolide fungicides prepared in example 1
| Pathogenic bacteria | Inhibition ratio (%) |
| Sclerotinia sclerotiorum | 69.08 |
| Wheat scab germ | 19.06 |
| Cucumber gray mold | 1.19 |
| Anthracnose of grape | 8.2 |
| Rhizoctonia solani of rice | 34.59 |
| Corn leaf spot germ | 39.13 |
| Botrytis cinerea (Fr.) Franch | 0 |
| Bacterial bakanae of rice | 5.93 |
| Rhizoctonia cerealis | 27.59 |
| Early blight of tomato | 8.07 |
| Verticillium dahliae of cotton | 4.37 |
| Magnaporthe grisea | 73.06 |
| Phytophthora capsici | 0 |
| Phytophthora sojae | 0 |
| Bacterial blight of rice | 95.18 |
| Bacterial leaf streak germ of rice | 84.85 |
| Cabbage black rot | 17.45 |
Example 4
The toxicity regression equation of the parthenolide bactericide prepared in example 1 was determined:
7 plant pathogenic bacteria with high parthenolide inhibition rate, such as sclerotinia sclerotiorum, rhizoctonia solani, corn microsporum, wheat rhizoctonia solani, rice blast, rice leaf blight, rice bacterial streak disease, and the like, are selected as test strains.
Indoor toxicity determination is carried out on 7 plant pathogenic bacteria by adopting a hypha growth rate method (fungi) or a turbidity method (bacteria). Specific method referring to example 3, a single concentration of parthenolide was substituted for 6 concentration gradients, whereas the virulence regression equation was calculated from the inhibition rate at each concentration using the software DPS v 7.05.
Test results
The regression equation of the toxicity of the parthenolide fungicide prepared in example 1 to each phytopathogen is shown in table 2. As can be seen from the results in the table, the parthenolide fungicide produced according to the technology of the invention has better drug effect on various pathogenic bacteria to be tested.
TABLE 2 As in example 1Regression equation of toxicity of prepared parthenolide bactericide to plant pathogenic bacteria
| Pathogenic bacteria | Regression equation of virulence | EC50 | EC90 | R value |
| Rhizoctonia solani of rice | y=3.7143+0.8209x | 36.83 | 1340.9 | 0.999 |
| Sclerotinia sclerotiorum | y=3.9850+1.0098x | 10.12 | 188.08 | 0.9733 |
| Rhizoctonia cerealis | y=3.0703+0.9997x | 85.17 | 1630.19 | 0.9959 |
| Corn leaf spot germ | y=2.9790+2.0180x | 10.03 | 43.31 | 0.9835 |
| Magnaporthe grisea | y=2.7819+1.0556x | 126.28 | 2067.44 | 0.9932 |
| Bacterial blight of rice | y=4.6054+2.0337x | 1.56 | 6.67 | 0.998 |
| Bacterial leaf streak germ of rice | y=3.4962+2.3432x | 4.38 | 15.44 | 0.9942 |
Example 5
In vivo efficacy tests of parthenolide fungicides formulated as in example 2 against several phytopathogens:
the test is carried out in a greenhouse cement pond of plant research institute of Chinese academy of sciences of Jiangsu province, the tested crop is rice, no chemical bactericide is used in the cement pond, and the tested objects are rice bacterial leaf blight and rice bacterial streak germ.
The experimental method comprises the following steps:
the test agents were parthenolide fungicides formulated in accordance with example 2, diluted with tap water to concentrations of 50, 100 and 200 μ g/mL, and clear water as a blank control, all of which were sprayed using a knapsack sprayer. The bacterial suspension of pathogenic bacteria is used for artificial inoculation one day before the medicine is taken, the medicine is sprayed for the second time 7 days after the medicine is taken, and after the control is fully developed, the disease condition is investigated and the control effect is calculated.
The test result shows that: under the treatment of the test agent, the bactericide with each concentration has no adverse effect on crops and grows normally. The aqueous emulsion prepared according to the embodiment 2 has good control effect on bacterial blight and bacterial streak of rice. The control effect on bacterial blight of rice is more than 85% and the control effect on bacterial streak of rice is more than 75% under the using dosage of 200 mu g/mL.
Claims (1)
1. Application of parthenolide in preventing and treating bacterial leaf streak of rice.
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